DOI: 10.5281/zenodo.
200633
Dossier – Can coatings
December 2016
1 Introduction
Canning of food and beverages allows their preservation for months
to years while maintaining taste and nutritional values. Metal cans are
generally coated with an organic layer protecting the integrity of food
cans from effects of the food. For example, highly acidic foods and
some food ingredients promote corrosion of metal leading to leakage
of the can and spoilage of the food. In addition, coatings prevent
reactions between the can’s metals and the food which could e.g.
result in unwanted cloudiness of beverages or staining of food. Can
coatings have to fulfill a variety of different technical and legal
requirements (Figure 1) [1, 2].
Ideally, can coatings should…
… be flexible enough to withstand forming of the cans.
… be universally applicable to all different food types.
… resist a wide temperature range, because food may be processed
in the cans at high temperatures and under pressure.
… not transfer constituents to food in quantities that endanger human
health.
… not peel off during can production, shelf-life and after non-
intentional deformation of the cans.
… withstand the chemistry of aggressive food types (e.g. acidic foods)
and protect the metal of the can from corrosion.
… preserve the flavor and appearance of food and maintain its
organoleptic properties.
… be stable over several years.
2 Can production
2.1 Can body
Food and beverage cans are made of three different materials [3, 4].
Firstly, aluminum which is light and ductile, but relatively weak and
which cannot be soldered. Aluminum cans have a wall thickness of
about 0.1 mm. Secondly, tin-coated steel (tinplate) which is usually
less than 0.5 mm thick and covered on both sides with a tin layer of
approximately 1 µm. Thirdly, electrolytic chromium coated steel
(ECCS) which is typically 0.2 mm thick and has a layer of chromium
that is in the low nanometer range. Tinplate and ECCS can be
soldered.
1 2 3 4
Figure 1. Can coatings should - 1 withstand the can manufacturing process, 2 be universally applicable to different food types and
withstand aggressive food types, 3 withstand the food sterilization process, 4 minimize the release of their constituents into food, 5
adhere to the metal, even after mechanical deformation of the can, 6 prevent corrosion processes, and 7 not change the organoleptic
properties of the food.
1
Birgit Geueke
Cans are formed from two or three pieces of metal according to three
main procedures:
 3-Piece welded cans (3PC): For three-piece cans, a rectangular
piece of coated tinplate is rolled into a cylinder and closed with a
seam, which is subsequently coated from the inside. The bottom
piece and the can body are joined by a process called double
seaming. After filling, a lid is also seamed on the top of the can
body.
 2-Piece drawn and redrawn (DRD) cans: Two-piece cans are
made from a coated aluminum or steel disk, which is first drawn
into the shape of a shallow cup. Several redrawing steps can be
performed progressively reducing the diameter and increasing
the height of the can. The surface area and the thickness of the
material remain constant during the process.
 2-Piece drawn and ironed (D&I) cans: Alternatively, two-piece
cans are formed by drawing an uncoated tinplate or aluminum
disk into the shape of a cup, followed by stretching and ironing
steps. The ironing steps typically reduce the wall thickness of the
can. These cans are coated on the exterior and interior after
production.
2.2 Can coating
Organic coatings are routinely applied onto the inside and outside of
food and beverage cans made of aluminum, tinplate, and ECCS. Most
coatings form thin films of 1 to 10 µm [5]. As an exception, tin cans
without internal coatings are used for light colored, acidic juices and
fruits (e.g. pineapple, pears, peaches). Under these conditions, tin is
more easily oxidized than the food, thus preventing darkening and
flavor changes caused by oxidation of the food.
For the majority of food and beverage cans, coatings are applied to
both sides of planar metal sheets or coils by roller coating before the
cans are formed [6]. This process is also used to coat the outside of
cylindrical can bodies. Alternatively, spray coatings are applied on the
interior of preformed 2-piece D&I cans and sometimes for 2-piece
DRD cans [4]. Can coatings often also serve as lubricants during the
production process.
5 6 7
Coatings are generally spread as suspensions in organic or aqueous
solvents. They are dried by solvent removal, oxidation or heat
polymerization, which is usually achieved by heating and/or UV
radiation. During this process (known as “curing”) cross-linking
reactions take place forming a three-dimensional network and giving
the coating the final properties [4]. In some cases, e.g. for sealing the
side seams of 3PCs, powder coatings are applied under the direction
of an electrostatic field and cured by heat.
Depending on the material and application, it is sometimes necessary
to use several layers of coatings, e.g. to overcome low adhesion to
the metal, secure high protection or introduce a functional barrier
preventing migration from the base coat.
Interior coatings are typically colored gold, white, gray or they appear
aluminized. Exterior coatings often have a clear or gold appearance.
Beverage cans are usually printed on their outside, whereas most food
cans have a printed label which is glued on using adhesives.
2.3 Canned foods and beverages
Canned foods include a large variety of vegetables, fruits, meat, and
fish, but also dairy products and ready meals. For sterilization, the
cans are filled, sealed and then heated under pressure for a certain
time whereas the exact conditions depend on the food type. Heating
up to 100°C without pressure is only sufficient for highly acidic foods
with a pH value below 4.5
Beverage cans are used for carbonated soft drinks, beer, juices, teas,
coffee, energy drinks, and others. Beverages may be pasteurized or
sterilized in the sealed cans or filled under aseptic conditions.
3 Coating materials
A large variety of can coatings are commercially available. They differ
in the main chemical compositions, production processes, costs, and
technical properties [3, 4, 7]. However, only a limited number of
chemical functionalities is used to produce these resins. The high
diversity of coatings is caused by variations and combinations of the
resins and further increased by the number of possible cross-linking
agents and additives [5]. The main types of resins are detailed in the
following sections and the cited information was retrieved from
references [3-5, 7-9], if not stated otherwise.
Box 1: History
 In the beginning of the 19th century, food canning methods were
developed with the aim to preserve large amounts of food. A first
tin can process was patented in 1810. The cans of the first
generation were hand-made and needed to cook for up to 6
hours.
 By the 1860s it was possible to manufacture smaller machine-
made steel cans. The time to cook food in such sealed cans was
reduced to thirty minutes.
 In the 19th century, tin cans were usually sealed with solder
containing high levels of lead. In the years 1845-48 and 1872-
73, two arctic expeditions ended dramatically with the deaths of
the entire crews. It was hypothesized that lead poisoning caused
by the consumption of canned food contributed to the failure of
these two expeditions [10, 11].
 Beer was successfully canned for the first time in the year 1933
[4].
 In the 1940s, synthetic coatings were developed and started to
be used in cans [3]. The use of epoxy coatings began in the
1950s [3].
2
3.1 Epoxy
Since the 1950s, epoxy-based resins became the most commonly
used class of coatings for aluminum and steel cans. In 2013, their
market share was estimated to be 95%. Epoxy coatings protect the
metal from corrosion, withstand a wide range of foods and resist heat
and acidic conditions. Additionally, they adhere well to different metal
surfaces and exhibit sufficient flexibility during most production
processes.
The most common epoxy coatings are synthesized from bisphenol A
(BPA, 1) and epichlorohydrin (2), forming bisphenol A-diglycidyl ether
epoxy resins (3).
Cl
+
O
HO OH
1 2
O O O O O O
OH
n
3
Many different blends of epoxy coatings have been developed with
epoxy-phenolic coatings being the most important subgroup. Other
blended resins are e.g. epoxy amines, acrylates, and anhydrides.
3.2 Oleoresin
First can coatings were made of oleoresins, which are mixtures of oil
and resin extracted from plants. Their use largely stopped with the
invention of epoxy coatings in the middle of the last century, but
oleoresins were rediscovered as BPA-free alternatives. Oleoresins
are rather flexible, but do not adhere well to metal surfaces. They are
easily applied, but need long curing times. The corrosion resistance
of oleoresin-coated cans is limited, which restricts their use to mild
foods e.g. different kinds of beans. Oleoresins have been reported to
change the organoleptic properties of food.
 In the late 1950s, aluminum beverage cans were introduced to the
market followed by 2-piece D&I cans in the late 1960s [6].
 Around 1960, epoxy-phenolic resins were invented that prevented
the migration of metal into sensitive beverages such as beer [4].
 In the 1970s, polyester-based can coatings became commercially
available. They were mainly combined with phenolic resins [12].
 In 1978, the use of polyester-urethanes for internal coatings started
[12].
 In 1995, the U.S. Food and Drug Administration (FDA) issued a
final rule prohibiting the use of lead-tin solder in food containers (21
CFR 189).
 In the late 1990s, oleoresin can coatings were re-introduced for
certain vegetables in the U.S. and Japanese companies started to
apply polyester-based alternative can coatings (including PET
laminates) on top or instead of epoxy coatings.
 In 2015, the use of bisphenol A (BPA)-based coatings in food and
beverage cans was banned in France (LOI n° 2010-729).
 In 2016, the U.S. food companies Del Monte and Campbell
announced the phase-out of BPA-based coatings by 2016 and
2017 at the latest, respectively.
3.3 Vinyl
Vinyl coatings are synthesized using the monomers vinyl chloride and
vinyl acetate. They exhibit excellent flexibility and are commonly
applied as a second coating layer (“top coat”), because they do not
adhere well on metal. The addition of stabilizers and plasticizers is
generally needed and vinyl coatings are often blended with other
resins to optimize their properties. Vinyl coatings are stable under
acidic and alkaline conditions, but do not withstand high temperatures.
These properties make them suitable for cans which need completely
unbroken films and are not sterilized after filling (e.g. soft drinks).
Vinyl organosols are prepared from suspensions of resin in organic
solvent. They also require plasticizers and stabilizers. Organosols
offer comparably higher chemical resistance, thermal stability, and
adhesion properties than vinyl coatings.
3.4 Phenolic
Phenolic resins are generally composed of phenols and aldehydes.
They are highly corrosion resistant and protect cans from sulfide
staining. Phenolics have low flexibility, do not adhere well to metal,
and may change the odor and flavor of some foods. They find
application as coatings for drums and pails, but unblended phenolic
resins are not used in food and beverage cans. However, phenolics
are common crosslinkers (e.g. in epoxide resins) and increase their
resistance against corrosion and sulfide stains.
3.5 Acrylic
Ethylacrylate is the most commonly used monomer to synthesize
acrylic coatings. Acrylic resins display corrosion and sulfide stain
resistance, but they are rather brittle which is a disadvantage during
production and processing. They have a clean appearance when
pigmented with titanium dioxide, but may change the organoleptic
properties of food. Because of these properties, they are commonly
used as external coatings. Acrylics and their blends are currently
under investigation as replacements for BPA-based epoxy coatings
[1].
3.6 Polyester
A wide variety of polyester resins can be synthesized by condensation
reactions between a polyvalent acid and polyalcohol(s) or epoxide(s)
[13]. Isophthalic acid (IPA) and terephthalic acid (TPA) are the main
carboxylic acids used in polyester coatings [12]. Polyester resins are
easy to handle during the production process and adhere well to the
metal surface. However, they are usually not stable under acidic
conditions and have a poor corrosion resistance. Therefore, they
cannot be used for acidic food types.
Alternatively, polyethylene terephthalate (PET) coatings are laminated
onto the inside and sometimes also the outside surface of non-welded
food and beverage cans (tradename aTULC) [14]. In these cases,
adhesives are needed to bind the PET laminate onto the metal.
Polyester-coated laminated cans were developed in Japan and
labeled “BPA-reduced cans” [15].
3.7 Polyolefins
Coatings that are based on dispersions of polyolefins have recently
entered the market and are sold under the tradename CanveraTM. The
development of a new technology allows the dispersion of high
molecular polyolefins in aqueous systems without the addition of
surfactants or emulsifiers. The final polyolefin coating exhibits
corrosion protection, adhesion, and flexibility without impacting the
flavor of the food, the manufacturer states.
3
3.8 Additives
Additives include agents to increase surface slipping as well as
abrasion and scratch resistance. Further additives are used to prevent
foam formation during production and to improve the adhesion of the
coating on the metal surface. Scavengers for hydrochloric acid are
especially added to vinyl-based coatings.
Lubricants are used to enable the can forming process, minimize
adhesion of food to the packaging and to enhance the elasticity of the
coating [16]. Waxes, paraffins, fats and oils, partial acyl glycerols or
fatty acid amides are commonly used for these purposes.
Protein-rich foods contain sulfur that may be released in the form of
free sulfide, hydrosulfide ions, and hydrogen sulfide gas during
processing and lead to unwanted organoleptic properties [4].
Additionally, sulfide may react with tin and/or iron leading to dark
stains inside the can. The addition of zinc oxide or aluminum pigment
helps to prevent such stains due to the formation of almost invisible
white metal sulfides. Titanium dioxide is another common additive
providing a clean white appearance of the coating and masking sulfide
stains because of its good hiding power [17].
4 Alternatives to epoxy coatings
Epoxy coatings combine several advantages such as universal
applicability, high stability, good processability, and low cost [6].
Nevertheless, food companies have started to replace BPA-based
epoxy coatings by alternatives in response to toxicological evidence,
public discussions, and recent regulatory decisions.
Already in 2013, patent filings and regulatory approvals by paint and
chemical firms showed that many new coatings were under
development [1]. Acrylic and polyester coatings are currently used as
first generation alternatives and, more recently, polyolefin and non-
BPA epoxy coatings have been developed with the aim to replace
traditional epoxy coatings [18, 19]. Other inventions developed to
reduce BPA migration include BPA capturing systems [20] and top
coatings [21]. Instead of replacing epoxy coatings, food manufacturers
may also decide to change completely to other types of packaging
(e.g. from cans to plastic bottles or composite cartons) [22].
Manufacturers introduced the term “bisphenol A non-intent” (BPA-NI)
for coatings that are based on other monomers than BPA [6]. With this
practice, they avoid labelling their products as BPA free, which would
be an ambitious aim due to the ubiquitous presence of BPA, but
instead claim that they do not intentionally add BPA.
Although several alternative coatings already exist, none of them
fulfills all the above-mentioned requirements of an ‘ideal’ can coating.
Therefore, alternative coatings can presently only be used with certain
limitations. Most of them are more expensive than epoxy coatings.
Furthermore, their use may reduce the storage time of foods because
the stability is not sufficient or it has not been adequately tested before
bringing onto the market. The latter shows an important difficulty in the
search for alternative coatings: Not only the research and
development, but also the testing phase of novel coatings contribute
to the long periods of time until a new material can be introduced into
the market. Additionally, suitable alternatives should be compatible
with many different food types, which extends the effort during the
testing phase even more [23] and lead to typical development times
of approximately ten years [24].
However, first evidence for the toxicological properties of BPA has
been published in the 1990s and the debate on the safety of BPA
intensified in the beginning of the 2000s [25]. The time elapsed
indicates that coating manufacturers may have missed an opportunity
to react faster and start to work on safer alternatives earlier.

5 Market data
5.1 Cans
Global estimates of recent years showed that more than 300 billion
beverage cans were produced each year and that the trend is
continuously increasing [6, 26, 27]. Furthermore, it was estimated that
approximately 75 billion food cans were produced globally in 2011
[26]. In 2014, 90% of the beverage cans were made of aluminum; the
remaining 10% consisted of steel [27]. Major global players of the
beverage can market are Ball (who acquired can manufacturer Rexam
in June 2016), Crown, MCC, and Can Pack [27]. The preferences for
beverage packaging strongly differed by region: Whereas more than
40% of beverages were sold in cans in the U.S. and Canada, this
value was between 10-20% in the rest of the world [6]. In 2013, 350
cans per capita were consumed in North America, followed by 80, 70,
17, and 2 cans per capita in Latin America, Europe, China, and India,
respectively [6].
In 2013, about US $30 billion and US $9 billion were globally earned
with beverage and food cans, respectively [6]. The global metal food
packaging market was estimated to be US $64 billion in 2014 and rise
to US $75 in 2019 [27].
5.2 Can coatings
In 2011, the global production capacity of can coatings was estimated
to be 800’000 metric tons, which corresponds to a market value of
€2.8 billion [28]. In 2013, another study assumed a global market
value of approximately $3 billion dollar for packaging coatings [6]. The
end-uses of coatings in the packaging market were beverage can
bodies (20-25%) and ends (10-15%), food cans (25-30%), and caps
and closures (5-10%) [6]. Approximately one third of the coatings were
used in non-food packaging. Global market leaders were Valspar,
PPG, and AkzoNobel who shared two third of the market for
packaging coatings [6]. Due to increased pressure to substitute BPA-
based epoxy coatings, many new substances are under investigations
by paint and chemical firms [1]. This development may significantly
change the coating market in future.
6 Regulation
6.1 Europe
In Europe, can coatings generally have to fulfill the requirements of
the European Framework Regulation EC 1935/2004 on food contact
materials (FCMs) [2]. In article 3, the regulation defines that FCMs
shall be manufactured “so that […] they do not transfer their
constituents to food in quantities which could endanger human health
or bring about an unacceptable change in the composition of the food
or […] deterioration in the organoleptic characteristics.”
Can coatings are not regulated by an EU-wide legislation, but specific
measures exist in several Member States. In the Netherlands,
coatings of FCMs are covered under the Dutch Packaging and Food
Utensils legislation. Chapter X includes nine different types of FCM
coatings, but various other chapters also comprise coatings. A
revision of all chapters dealing with coatings is currently in progress
and may lead to three new parts concerning (1) general provisions,
(2) general-purpose coatings, and (3) coatings for specified
applications. In the Netherlands, can coatings continue to be regulated
based on a positive list of substances in future. They will belong to the
general-purpose coatings. Other Member States with national
regulation on can coatings in place are Belgium [29], Czech Republic,
Greece, Italy, Slovakia, France and Spain [30-32].
Few chemicals that are known to have the potential to migrate from
cans and coatings into food are specifically regulated in the EU:
 Specific migration limits for bisphenol A diglycidyl ether (BADGE,
4) and its derivatives were defined in Commission Regulation EC
4
1895/2005 [33]. BADGE and its hydrolysis products BADGE·H2O
(5) and BADGE·2H2O (6) shall not exceed a group specific
migraton limit (SML) of 9 mg/kg food. The SML is based on a
tolerable daily intake (TDI) of 0.15 mg/kg. A second group SML
of 1 mg/kg food was assigned to the three chlorohydrins of
BADGE (BADGE·HCl (7), BADGE·2HCl (8), BADGE·H2O·HCl
(9)). The use of bisphenol F diglycidyl ether (BFDGE) and
novolac glycidyl ether (NOGE) in FCMs was not authorized due
to the lack of toxicological data. However, BFDGE and NOGE
were permitted in the coating of large containers intended for
repeated use. For such applications, no migration limits were set.
O O O O O O O OH
4 7 Cl
O O OH HO O O OH
O
5 OH Cl 8 Cl
HO O O OH HO O O OH
OH OH OH Cl
6 9
 Regulation EC 466/2001 on setting maximum levels for certain
contaminants in foodstuffs was amended by Commission
Regulation EC 242/2004 regarding inorganic tin in foods.
Accordingly, tin concentrations of 200, 100, and 50 mg/kg food
shall not be exceeded in canned food, canned beverages, and
products for infants and young children, respectively.
 In the beginning of 2016, the European Commission (EC)
published a draft regulation on the use of BPA in varnishes and
coatings as well as an amendment of the plastics regulation
(Commission Regulation EU 10/2011). An SML of 0.05 mg/kg
food is proposed for coatings and varnishes. The current SML of
0.6 mg/kg food as defined for plastic FCMs shall be reduced to
0.05 mg/kg food, too.
 In January 2015, France banned the use of BPA in FCMs
including all packaging, containers and utensils intended to come
into direct contact with food (LOI n° 2010-729). In September
2015, the French Constitutional Council decided to partially lift
the ban on the manufacture and export of BPA-containing FCMs,
while the ban remains valid at national level.
6.2 United States
In the U.S., polymeric and resinous coatings are generally covered
under 21 CFR 175.300. This code lists permitted starting substances
and specifies test conditions and migration limits. Can coatings
meeting these specifications are compliant with the law.
A specific legal measure concerning can coatings exists in California
[34]. In May 2015, California’s Office of Environmental Health Hazard
Assessment (OEHHA) added BPA to the list of chemicals known to
cause reproductive harm under Proposition 65. As a consequence,
manufacturers, distributors, and retailers have to inform the
consumers of BPA-containing products with a clear and reasonable
warning regarding the chemical hazards. In May 2016, OEHHA
proposed a temporary point-of-sale warning label for canned and
bottled food and beverages. By the end of 2017, products containing
BPA are required to be directly labelled.

7 Migration
The majority of studies about chemical migration from food cans
focused on epoxy coatings and the migration of BPA, BADGE and
their derivatives. However, many other substances may migrate from
all different types of can coatings, e.g. oligomers, catalysts, reaction
accelerators, epoxidized edible oils, amino resins, acrylic resins,
various esters, waxes, and lubricants [35].
7.1 Test conditions
In Europe, no harmonized legislation regulates the use and testing of
coated metal cans. Standardized test conditions were published in the
standard CEN/TS 14235:2002 (“Polymeric coatings on metal
substrates - Guide to the selection of conditions and test methods for
overall migration”). Due to the lack of further legal guidelines,
companies also apply the testing guidelines for plastics, although the
typical filling, processing, and storage conditions strongly vary
between plastic food packaging and food and beverage cans.
Whereas cans are often hot-filled or even sterilized, plastic packaging
materials are generally not heated during packaging. Also, the storage
times may differ significantly: food cans have typical shelf-lives of 2-5
years leading to very long contact times between the packaging and
the food.
The FDA currently recommends migration test conditions including a
retorting step at 121°C for 2 hours followed by storage for 10 days at
40°C to evaluate the safety of cans. In a recent study, the migration
from polyester can coatings was measured up to 515 days [36]. Based
on the results, the authors suggested to modify FDA’s test protocols
for new can coatings to be able to adequately address long-term
storage and monitor ongoing hydrolysis and interactions between the
coating and the filling of the can. Migration studies from vinyl coatings
supported this proposal to modify the current test conditions [37]. The
finding of appropriate food simulants and the measurement of
migrants directly in the food were identified as further challenges [36].
7.2 Overall migration
In the 1990, the values for overall migration from food cans were
typically in the range of 1-5 mg/dm2, but sometimes even exceeded
10 mg/dm2 [35, 38]. As a consequence, Grob et al. proposed an
overall migration limit of 0.3 mg/kg food for the sum of
unknown/untested migrants below 1000 Da [39]. Many migrants from
all different can coatings belong to the group of non-intentionally
added substances (NIAS), which may be structurally and
toxicologically characterized or even completely unknown [40].
7.3 Specific migration
Bisphenol A (BPA) from epoxy coatings
Since the late 1990s, numerous studies from all over the world
demonstrated that the occurrence of BPA in epoxy can coatings and
its migration from such coatings into food and beverages are common
phenomena (e.g. [21, 41-61]). Migration of BPA mainly occurred
during can processing, sealing and sterilization, and less during
storage or after can damage [62].
Bisphenol A diglycidyl ether (BADGE) and its derivatives
BADGE is used as intermediate during the production of epoxy
coatings [38]. Furthermore, BADGE has commonly been added to
organosol coatings as scavenger for hydrochloric acid which is formed
as unwanted by-product after exposure to heat [63-65]. In the late
1990s, first studies were published showing the migration of BADGE
into canned fish, regularly exceeding levels of 1 mg/kg food [35, 38,
66-68]. Since then BADGE has continuously been measured in
canned food and beverages [50, 61, 69].
5
Depending on the intended function of BADGE and the production and
storage conditions of the can, different reaction products are formed
[70]. The epoxy groups of BADGE can hydrolyze in the presence of
water to BADGE·H2O (5) and BADGE·2H2O (6). When BADGE is
used as scavenger for hydrochloric acid or in the presence of salty
food, BADGE·Cl (7), BADGE·HCl·H2O (9) and BADGE·Cl2 (8) are
formed. Furthermore, a cyclic product (cyclo-diBA, 10) is a common
by-product from BPA and BADGE during the production of epoxy
resins [35, 71]. The migration of many different BADGE derivatives
was described in various publications, e.g. [49, 70, 72-74]. In general,
the total migration of BADGE and its derivatives was higher from
organosols than from epoxy coatings because of its different functions
in the two materials [72].
In 2010, more complex reaction products of BADGE with food
ingredients such as sugars and peptides were identified [75]. The high
reactivity of BADGE’s epoxy group explains the commonly observed
decrease of BADGE during storage and leads to increased diversity
of unknown molecules in the food [75].
O O O
O O O
12 p,p
HO OH
O O
O O
O
O
12 o,p
10
O O O O
HO OH
11 p,p
12 o,o
Novolac glycidyl ether (NOGE) from organosol coatings
In the U.S., NOGE has commonly been used as scavenger for
hydrochloric acid in organosols; in the EU, it has replaced BADGE for
certain years until regulatory action banned the use of NOGE in can
coatings [64]. NOGE is a complex mixture of epoxidized molecules
based on the three isomers of bisphenol F (p,p-BPF (11), o,p-BPF,
o,o-BPF) and its 3- to 8-ring derivatives[33, 64]. NOGE typically
contains 30-40% BFDGE. In 2001, 5.6 mg/kg NOGE was measured
in stuffed peppers packaged in food cans [64]. Migration of BFDGE,
which is usually present in three isomeric forms (p,p-, o,p- and o,o-
BFDGE (12)), and further NOGE-related compounds was measured
in various other studies [49, 69, 74, 76]. In some cases, concentrations
of BFDGE and its derivatives reached levels above 1 mg/kg food [68,
77].
BPF is also formed from white and yellow mustard seeds under certain
production conditions and was detected in 48 of 61 samples of mainly
mild mustard from the Swiss market [78].
Oligoesters
Linear and cyclic oligoesters belong to the common non-intentional
by-products of polyesters [13]. Analyses of total migrates showed that
up to 50% of the migrate consisted of such oligoesters, typically at
concentrations below 1 mg/dm 2 [12]. The variety of monomers used
in coating polyesters makes the prediction, analysis and quantification
of oligomers very challenging and analytical standards are generally
not available yet [79]. Hydrolysis of some high molecular weight
polyester compounds after long-term storage was demonstrated and
may complicate the analysis even more [36].
Attempts to minimize the migration from polyester coatings led to the
development of polyester-polyurethane coatings. However, a broad
variety of different oligomers, plasticizers, surfactants and impurities
were identified in the migrate of these materials [80].
Crosslinkers
Trimellitic acid (TMA), melamine and benzoguanamine (BGA) are
used as cross-linkers in e.g. epoxy- and PVC-based coatings. In 2004,
migration of more than 1 mg TMA and its possible derivatives per kg
food was reported from cans purchases at the Swiss and Austrian
market [81]. Under standard retorting conditions, melamine migration
up to 0.4 mg/kg food was measured from epoxy-based coatings [82].
BGA migrated from PVC-coated food cans and reached levels up to
84 µg/dm2 after 1.5 years of storage at 40°C [37].
Lubricants
The sum of migrating lubricants was reported to be 0.3 mg/dm 2 and
5.5 mg/dm2 from epoxy-anhydride coatings and polypropylene films,
respectively [16].
Metals
Metals are common migrants from non-coated and/or dented cans.
Steadily increasing migration of iron into pineapple juice was reported
for dented cans reaching maximum iron levels of 14.4 mg/L after one
year of storage at room temperature [83]. Other exemplary studies
reported migration of e.g. lead and iron into chickpeas [84], aluminum
into tea and beer [85], and tin into different food types [86].
8 Exposure and biomonitoring
8.1 BPA
Exposure studies from all over the world showed the contribution of
canned food and beverages to BPA exposure, e.g. [15, 21, 48, 51, 53,
54, 58, 87]. Two review articles from 2007 and 2011 judged that BPA
migration from cans strongly contributed to human BPA exposure [88,
89]. In 2015, the European Food Safety Authority (EFSA) concluded
in its most recent scientific opinion on BPA that a large majority of food
categories contained higher levels of BPA in canned than in non-
canned food [90]. Seven out of 17 canned food categories exceeded
average BPA levels of 30 µg/kg (grain and grain-based products,
legumes, nuts and oilseeds, meat and meat products, fish and other
seafood, herbs, spices and condiments, composite food, and snacks,
desserts, and other foods), whereas average BPA concentrations in
canned beverages remained below 3 µg/kg [90]. In 2016,
biomonitoring data confirmed this observation: According to an
analysis based on the National Health and Nutrition Examination
Survey (NHANES), urinary BPA levels were increased for people who
regularly consumed canned food, whereas the consumption of
canned beverages did not show a correlation with urinary BPA levels
[91]. Another comparison of general BPA exposure with biomonitoring
data led to the identification of canned foods as potentially important
BPA exposure source for children [92].
8.2 BADGEs and BFDGEs
A second, common group of migrants from can coatings are BADGE,
BFDGE and their derivatives. In 1999, exposure to BADGE was
estimated to be 0.7 mg per person and year based on concentrations
6
measured in canned fish [93]. In 2013, the exposure to cyclo-diBA
from food cans was assessed [71]. Based on Swiss consumption data
and the maximum concentrations measured in canned fish, it was
concluded that high consumers of canned fish could easily exceed
safe cyclo-diBA levels. In 2012, first biomonitoring data for BADGE
and its derivatives (BADGEs) showed that the urinary concentrations
of BADGEs in the U.S. population exceeded those of BPA by 3 to 4
times [94]. The occurrence of BADGE was also reported in Indian
children [95] and in the Greek population [96]. In 2015, first results
were published on the occurrence of BFDGE and its derivatives
(BFDGEs) in human blood and adipose fat [97]. BFDGEs
concentrations were generally higher than the total concentration of
BADGEs. However, a positive correlation was seen between the
concentrations of BFDGEs and BADGEs. BADGE and BFDGE are
designated chemicals for the California Environmental Contaminant
Biomonitoring Program [98].
9 Toxicity
9.1 Bisphenols and derivatives
Toxicity data for BPA are extensive and cover many different
endpoints such as reproductive and developmental effects as well as
neurological, immune-modulatory, cardiovascular and metabolic
effects [25, 90, 99-105]. Although there are ongoing controversies on
the interpretation of this information, BPA’s toxicity, especially its
reprotoxic properties, are widely recognized by different authorities
([106], Annex VI of [107], [108]).
In 2004, the toxicity of BADGE was reviewed and it was concluded
that it neither affects reproduction and developmental endpoints nor
acts as endocrine toxicant [109]. In the same year, EFSA concluded
in a scientific opinion that BADGE and its derivatives do not raise
concern for genotoxicity and carcinogenicity in vivo [110]. However,
more recent studies showed effects of BADGE e.g. on the testes of
rats [111], on adipocytes in vitro [112], and on the development of
amphibians [113]. The lack of toxicity data for NOGE and BFDGE led
to the prohibition of their use and presence in FCMs in Europe [33].
In 2016, an epoxy coating based on tetramethylbisphenol F (TMBPF,
CAS 5384-21-4) was introduced to the market. Toxicity tests which
were published by the manufacturer did not show any evidence for
endocrine activity and genotoxicity [114].
9.2 Total migrates/extracts
Besides the well-known migrants BPA and BADGEs from epoxy-
coatings, can coatings generally release a far more complex mixture
of substances into the food [39, 71]. Many of these substances are
neither structurally identified, nor toxicologically tested, nor routinely
analyzed. However, they may strongly contribute to the total toxicity of
the migrate. In 2006, cytotoxic effects of migrates from epoxy- and
polyester-based coatings were tested using a series of assays [115].
The results of one of these assays showed that only about 0.5% of the
cytotoxic effects measured in the migrate from epoxy coatings could
be traced back to the amount of BPA, BADGE and BADGE·H2O. This
example illustrates the importance of tests targeting the final migrate
and not only single substances during risk assessment.
Abbreviations
3PC 3-Piece welded cans
BADGE 2,2-Bis(4-hydroxyphenyl)propane bis(2,3-
epoxypropyl) ether
BADGEs BADGE and its derivatives
BFDGE Bisphenol F diglycidyl ether
BFDGEs BFDGE and its derivatives
BGA Benzoguanamine
BPA Bisphenol A
BPA-NI Bisphenol A non-intent
cyclo-diBA Cyclic product formed from BPA and BADGE
D&I Drawn and ironed
DRD Drawn and redrawn
EC European Commission
ECCS Electrolytic chromium coated steel
EFSA European Food Safety Authority
FCMs Food contact materials
FDA U.S. Food and Drug Administration
IPA Isophthalic acid
NHANES National Health and Nutrition Examination Survey
NOGE Novolac glycidyl ether
OEHHA Office of Environmental Health Hazard Assessment
PET Polyethylene terephthalate
PVC Polyvinylchloride
SML Specific migration limit
TMA Trimellitic acid
TMBPF Tetramethylbisphenol F
TPA Terephthalic acid

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7
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